5 underappreciated skills for leading digital transformation

Let's talk about the power of a well-placed question – and other underrated skills for leaders doing digital transformation work
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In 2006 I got my first job in IT, running a support team and a software testing team. I didn’t have a technology background: In fact, I changed majors from computer science to math after just one semester of college. I remember that I would sit in team meetings and nod along as projects were described and software development plans were made. And then, immediately following, I would grab a trusted friend, head to a private office, and get them to explain it all to me. People who advanced in IT in 2006 were those who understood all about the bits and bytes, network speed and databases, storage arrays and HTML - all the things that were foreign to me.

I saw people who were experts in their technical fields but couldn't effectively lead a team or deliver critical projects.

As the years progressed, I recognized that while the technical skills were important, they weren’t all that was needed to be successful. I saw more and more examples of people who were experts in their technical fields but just weren’t able to effectively lead a team, influence business partners, or deliver critical projects. I began calling upon those non-technical skills and started to advance to more senior IT leadership roles.

Fast forward to 2019 - I’m still in IT and, while I’ve improved my technical acumen, I use my non-technical skills daily. I have a masters in college student development and counseling and am a trained business and executive coach. The skills I learned in these programs and through my years in leadership roles, both inside and outside of IT, have been invaluable as IT evolves and digital transformation becomes the norm. Practicing and perfecting the skills below will help IT leaders influence both inside IT and across the business, and take digital transformation to the next level.

1. Read the room

Much has been written over the years about emotional intelligence and the advice primarily focuses on having a clear understanding of yourself, your emotions, and what motivates you. However, understanding not only yourself but also all the “players” in various situations has become more and more important. Using social intelligence to read people’s reactions, understand non-verbal queues, engage all team members and listen actively are necessary to make traction on key digital transformation initiatives across the company. Honing and using these skills allow IT leaders to avoid problems, engage the team, and ultimately keep things moving in the right direction.

2. Tell a compelling story

Using reason and data alone won’t get the job done.

Because technology is not solely in the realm of IT anymore and technology decisions involve people across the business, you will need to get more people on board with changes and transformation. Using reason and data alone won’t get the job done. Research shows that listening to stories puts your whole brain to work, not just the verbal processing portion. Tapping into your co-worker’s emotions through stories and anecdotes can influence stakeholders, forge connections andcreate momentum for your key initiatives. Storytelling can be as simple as an anecdote about a trip to the grocery store or as personal as talking about how you ran your first marathon - finding ways to get past the data allow you to connect in a meaningful and memorable way.

3. Make connections

Making connections to support transformation is more than just traditional networking. It’s about connecting people to one another, connecting ideas, and connecting strategies - enabling a 1 + 1 = 3 mentality. An IT leader in 2019 needs to see beyond their particular scope of responsibility to the big picture for the company and be aware of these critical connections. Whether that means introducing people so they can learn more about how their work impacts one another or facilitating a meeting to discuss the connection points between key initiatives, this ability to be a connector is an invaluable skill. IT leaders must look for opportunities to reach outside their team to make the most of the power of connection and collaboration.

4. Ask great questions

One critical skill I learned as a coach is the power of a well-placed question. We’ve all learned the difference between closed and open questions, but using open questions is sometimes not enough to garner the engagement, support, and actions necessary to move the ball forward. Great leaders ask provocative questions. Consider these:

  • “What’s keeping you from achieving that?”
  • “What is the most important thing to focus on right now?”
  • “What does success look like?”
  • “Do you need to work harder or delegate this?”
  • “Why does it matter?”

Focusing on getting people to think differently can unleash creativity and problem-solving in truly impactful ways. Whether you are talking one on one or leading a team through a difficult project, leading through questions can help your team to grow in ways you hadn’t imagined.

5. Learn even more about the business

During digital transformation, IT people are sitting at the table with salespeople, finance, marketing, R&D and others in the business, and are expected to understand the mission of the company and how the business operates. The business is looking for IT leaders to solve problems, not just implement technology, and this requires a clear understanding of the strategic direction of the company and using this knowledge to shape solutions that are tailored to the company’s specific needs.

Spend an afternoon shadowing a salesperson, sit in on a design review meeting for a new product line, or research your company - and its competitors - to better understand the market. This knowledge will equip you with critical insights that will help create impactful solutions for the company.

While technical skills will always be in demand, building a portfolio of skills that allow you to connect, inspire, problem-solve and drive transformation will enable IT leaders to be invaluable members of the business.

[ Read also: Teaching an elephant to dance - a free eBook on the six stages of digital transformation. ]

Stephanie Welsh has been at Red Hat for over five years and is the Senior Director for IT Strategy and Enablement.  In this role, Stephanie leads a team focused on enabling the business of IT to accelerate Red Hat’s overall strategy.  Her team includes portfolio management, financial management, enterprise service management, enterprise digital adoption, change management, process improvement,


Stephanie, where have you been all my life? Both of my degrees are in psychology, but I stumbled into and fell in love with finance and technology. I'm trying to bolster my IT knowledge, but that doesn't dim my belief that soft skills (especially people skills) are vital in this industry. Thanks for the wise words!